Unable to reorganize video playlists after a certain point

I have assembled a playlist of all canon star trek & star wars films/episodes.
I’m trying to put them in “chronological” order (story-wise, not release date).
It seems that after a certain number of entries in a playlist is reached you can’t reorder it any longer.
I’ve seen people mention this issue in the past (thread is now closed) but I have yet to see a solution.
Advice on fix, workaround, third-party solution, etc. would greatly be appreciated.
Thanks!

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